methyl (1R,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-propan-2-ylcyclopent-2-ene-1-carboxylate | 625099-11-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: methyl (1R,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-propan-2-ylcyclopent-2-ene-1-carboxylate
• CAS: 625099-11-8
• 化学式: C₁₅H₂₅NO₄
• 分子量: 283.368
• InChiKey: RLZMMJZCRLNHGF-IAQYHMDHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1R,4S)- N-BOC-4-氨基环戊-2-烯甲酸 在 potassium carbonate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 methyl (1S,4S)-4-[(tert-butoxycarbonyl)amino]-1-isopropylcyclopent-2-ene-1-carboxylate 、 methyl (1R,4S)-4-[(2-methylpropan-2-yl)oxycarbonylamino]-1-propan-2-ylcyclopent-2-ene-1-carboxylate
  参考文献：
  名称：

  Discovery of INCB10820/PF-4178903, a potent, selective, and orally bioavailable dual CCR2 and CCR5 antagonist

  摘要：

  We report the discovery of a potent, selective, and orally bioavailable dual CCR2 and CCR5 antagonist (3S,4S)-N-[(1R,3S)-3-isopropyl-3-({4-[4-(trifluoromethyl)pyridin-2-yl]piperazin-1-yl}carbonyl)cyclopentyl]-3-methoxytetrahydro-2H-pyran-4-amine (19). After evaluation in 28-day toxicology studies, compound 19 (INCB10820/PF-4178903) was selected as a clinical candidate. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.015

文献信息

• Benzoxazinyl-amidocyclopentyl-heterocyclic modulators of chemokine receptors
  申请人：Goble D. Stephen

  公开号：US20070238723A1

  公开（公告）日：2007-10-11

  Cyclopentyl compounds linked to a benzoxazinyl group through an amido moiety utilizing the ring nitrogen of the benzoxazine, and further substituted with a heterocyclic moiety, such compounds represented by formula I: which are used to modulate the CCR-2 chemokine receptor to prevent or treat inflammatory and immunoregulatory disorders and diseases, allergic diseases, atopic conditions including allergic rhinitis, dermatitis, conjunctivitis, and asthma, as well as autoimmune pathologies such as rheumatoid arthritis and atherosclerosis; and pharmaceutical compositions comprising these compounds and the use of these compounds and compositions.

  环戊基化合物通过酰胺基团与苯并噁唑基团相连，利用苯并噁唑环的环氮原子，并进一步用杂环基团取代，这些化合物由式I表示： 用于调节CCR-2趋化因子受体，以预防或治疗炎症和免疫调节性疾病和疾病，过敏性疾病，包括过敏性鼻炎，皮炎，结膜炎和哮喘，以及类风湿性关节炎和动脉粥样硬化等自身免疫病理病变；以及包含这些化合物的药物组合物和这些化合物和组合物的使用。